The Vicious Cycle of My Adult Professional Life

One of my longtime readers Taylor Lee left a comment that said what most people in my life tell me over and over again —

Not to be harsh, but I feel like you cycle through the same issues over and over again regarding work, depression, family anxiety, etc.

My advice is to break the cycle by choosing the path you haven’t taken before:
(1) Get a job at a bigger company. I think this will help solve a LOT of the problems you’ve been having with start-up life. Preferably some place near to where you live so your awful commute gets shortened.
(2) Figure out what triggers your anxiety/depression and what you can do to mitigate it. Whether it’s diet, exercise, more sleep, medication, therapy (I think you might benefit from CBT), your #1 goal should be getting your mental health on track.

I want to address both of these suggestions as they are good ones, but also aren’t necessarily solutions to the problem.

Get a job at a bigger company. Is startup life the problem? Maybe. In my 10 or so years in the workforce, only six months were spent in a company larger than 100 employees. In the six months I spent in that larger company I witnessed so much inefficiency and bad middle management getting away with practically murder, I promised myself I would never go back to a large company. In between then and now I have applied for roles at larger companies – knowing that one poorly run large company does not make them all bad – but my experience in startups means my job prospects in larger companies are moot. Larger companies tend to look for someone with very specific experience in one area, whereas startups value that I’m a bit of a jill of all trades.
I just honestly haven’t had any luck with even getting interviews at larger companies – whereas startups see me as the perfect fit (at least on paper.) I did get one job offer from a 300 person startup – which maybe would have been better – but in this case I did not feel I had the experience needed to lead the team I was going to be given and the stress would have been even worse. I also received a job offer for a poor-performing smaller public company that made business software which reminded me why I disliked larger companies in the first place – people pretended to be passionate about their products but you could tell they were just completely burnt out because they didn’t care. I checked a few months later and most of the people I interviewed had left the company (given its poor performing stock it may not have been by choice.)

This would likely be different at a consumer-focused public company, but I’m far too unqualified for these roles to land so much as an interview. Believe me, I’ve tried. I can keep trying and maybe eventually something will stick. It isn’t even the money anymore (big companies would pay significantly less since I’d be in lower level roles with less responsibility) – it’s just the reality that no one will hire me at a larger company – at least one I’d actually want to work at.

Figure out what triggers my anxiety/depression. Well, I’ve figured this out, and there’s a lot of things…

Doing a job where I’m supposed to know what I’m doing on day one and there is no room to be developed or to get better at what I’m doing before I’m judged and thrown to the curb (ok, this is a startup thing.)

Being responsible for too many things at once without clear definitions of what those things are (i.e. unlimited number of things I can do, and not knowing whether to focus on the few things I know how to do well, or spend time on the things that I know will add a lot of value that I don’t know how to do well, so I spend too much time on them and get extremely anxious over them versus being product)

Having to be social on a daily basis with the same people. This pretty much will be an issue in any office environment. As I’ve noted before I’m an ENFP with massive social anxiety, so over time a “work from home” job would also be draining… I need human contact. But having to be the person who makes that contact on a regular is anxiety causing. I often think it would be much better to be an engineer because it’s a given that you’ll be socially awkward and that makes it easier.

Work hours. I am not a morning person. My ideal situation would be working 11am to 7pm. Well, now I work about 8am to 7pm. If I work for a bigger company it’s unlikely my hours would get any better – right now I theoretically take an 8:30 train and get in at 10. If I worked at a big company job closer to home I likely would have to be in at 9, so the commute would be shorter but the time to wake up would be the same. I might get home earlier, which would be nice, but doesn’t help matters as I want to be able to sleep in and work later if possible. I guess if I get to leave at 5 everyday, if that exists in big companies, then maybe getting to work at 9 would be fine. But even bigger companies require long hours.

Work location. If I could work two days from home that would be hugely helpful. That way I could get a few days of social interaction but also have time to just focus on getting my work done. I think this would be the ideal situation.

Money. Whether I’m paid too much or too little when working for a business I’m always anxious about money. I’m anxious about it for many reasons. One, it’s ridiculously expensive to live where I live and my soon-to-be husband does not make enough to cover what we need to live a comfortable life here. I estimate that to afford a comfortable family life in the Bay Area you need to make at least $300k as a couple and even that is tight. So if I make $200k and he makes somewhere close to $100k, we might be ok. He’s at more like $60k right now and I’m a bit under $200, but we’re getting closer. I’ve saved a lot right now which is great but I’m now at the age where I’m about to have kids (if my body allows me to) and the numbers don’t add up if I take a lower paying job. Can we live on less money? Of course we can. A two bedroom apartment here will set us back $36k a year. Beyond that we can cut costs on food and clothes and entertainment. Lots of people survive on less. But I don’t want to. I want to have a comfortable middle class life. I want to buy a house or at least have an apartment in a safe area that feels like a home and not a temporary residence. I could go and make $140k and that’s still a great salary — and maybe that’s fine. Together we’d make $200k and we should be able to live on that. But will a $140k job really be that much less stressful than a $200k job? It might be. But then if I want to actually get back to $200k+ salary I’ll just have to move into more stressful positions and I’ll end up back where I started, only at that point I’ll be so deeply handcuffed to the lifestyle and supporting a family that I won’t be able to just pick up and leave or check myself into a mental institution.

Lack of completion. I really like jobs which are projects that have a beginning, middle and end to them. Without a sense of completion, I am extremely stressed out. And those projects must be substantial enough that my boss and peers see that there was significant effort put forth to do this thing and it was done and we all agree it was done well. I need that in my life to feel ok.

Not being trusted/respected to do what I was hired to do. I guess this is a double-edged sword… either the person who hires me doesn’t trust me and then I am constantly feeling judged or the person trusts me a lot and then I eventually cannot do the things they trust me to do and then they get very upset at me… but they were delusional in the first place to think I’d be able to solve all of these problems. But not being trusted is worse. But then I don’t exactly earn trust given that I tend to over commit to things and deserve that lack of trust. It’s just when I start out not being trusted, it’s a deep hole to dig out of… and so much of the trust stems from the ability to pretend like you have your shit together and everything is fine. And I’m the exact opposite of that where I am just too honest and will tell you when something is an issue and explain why. And this is going to be a problem in bigger companies even more than it is in smaller ones. In bigger companies it’s less about 1:1 relationships and more about politics, which is a game I can’t and don’t play.

What can I do to improve my mental health? Sleep? Diet? Exercise? Therapy?

All of the above.

I know when I sleep I feel better and less depressed/anxious. But I don’t sleep enough. I go to sleep at 1am and wake up at 6am and still end up late for work because I’m too anxious to move despite doing work in bed.

Eating healthy helps a lot. As does exercise. But when I exercise at 6am I lose out on sleep so I think it kind of offsets its productivity.

Therapy… I have a love-hate relationship with therapy. I’ve been to so many therapists I know that it’s a huge time and money suck with no successful outcome. It’s sanity maintenance which has value in and of itself, but not for how much it costs. Yes, I make a lot of money and yes, I can afford to spend it on therapy ($700-$1000 a month for 4 sessions) but then I end up anxious over the value of those sessions. It’s so expensive and this year I decided to put my money into personal training ($600/month) – my physical vs my mental health – because I’ve spent so much on therapy to date and where has it gotten me?

I’m not on any antidepressants and maybe I should be, but I know that sleep and diet and exercise all can help me be a lot less stressed and sad all the time. Drugs don’t change my work situation.

So… do I need to address these issues and make a significant change to my life soon? Yes. How? I don’t know. I’m spending all my money on my wedding right now – which is stupid but it is what it is – and then I’ll have time to figure out what to do with my life.

An old boss of mine from my journalism days offered to review a freelance pitch from me if I had any ideas – so I just sent one off and I haven’t felt this engaged and motivated about a potential paid project in a long time. I have no idea if they’ll accept my pitch but I’d love to get back into non-business journalism where I’m writing about issues that actually help people and represent those who do not have a loud enough voice to be heard. But I can’t make a living doing that, so it’s only a fun side project for now – but pitching the story this morning was rewarding in and of itself.

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5 comments

I got my most recent job by attending a women in tech conference and putting myself out there/talking to everyone I met. Networking truly works apparently!
Don’t be too hard on yourself. I think we all go through anxiety, bad behaviors, cycles of doing well and cycles of not doing well. It’s pretty normal. I have ups and downs. When we write blog posts though, we just capture our feelings in that certain time period. It’s an in the moment thing.

I’ve had similar experiences in that I always seem to get steered into startups and have struggled to even get interviews at larger companies. Many years ago, when I was very, very young, I had a choice between two offers–one with a startup and one with a larger company. I picked the startup since it seemed to offer more potential for growth–but I seemed to get tagged with the “startup” label and that has stuck with me throughout my career.

Working for a startup once or twice when you are young or haven’t done so before can be exciting–but I find it gets old pretty fast. In a startup there is always this pressure to “change the world”. It isn’t enough to simply make a solid contribution–if the startup doesn’t have a story about how they are going to “change the world”–preferably a story that can be delivered in a 15 second “elevator pitch”–they don’t get funded. If they’ve already been funded and their story becomes less compelling they don’t get any more funding rounds.

This continual pressure to “change the world”–which I don’t think people in larger companies or different walks of life experience even though I’m sure they have stressful jobs too–can be psychically exhausting after awhile. I’ve found that–while I’ve never really worked for a big company–I get more stable roles in other areas of the country than Silicon Valley.

Silicon Valley is an area that I’ve left and returned to multiple times in my career. It is clearly the epicenter of my career but while it is the most exciting place to be, I’ve always found more financial stability–and more respected job roles–elsewhere. In the Valley if the startup fails (and most do) all your hard work often just gets thrown away. Where is the job satisfaction in that?

I’ve also tended to make more money outside of the Valley. I don’t just mean that my income goes further elsewhere. I mean that in absolute dollar terms I usually command a higher salary elsewhere–the fact that the cost of living is usually lower elsewhere too makes it a double win financially to live elsewhere. In the Bay Area startup scene it can be difficult to ask for more money because everyone needs to buy into the fiction that the company will “change the world” and make everyone rich–if you ask for too much money it can be interpreted as expressing doubt in the “Kool Aid” they want you to drink. (No coincidence, IMHO, that the original “Kool Aid” guy, Jim Jones, lived in the Bay Area before moving his flock to Guyana. Something about the area seems to have long inspired this kind of sometimes dangerous thinking.)

Don’t get me wrong–I love the energy of the Bay Area and still enjoy visiting whenever I get the chance. But it’s never been particularly good for my career to live there and I’ve always found more stability elsewhere.

Well, what I’ve noticed after reading your blog for a long time is that you definitely get pulled into the same type of situation in your professional career, and it’s my opinion that you get way too focused on the compensation end of it. In at least your last two searches, you went from ‘Maybe I should consider taking a job down a different path though I’d make less money’ but ended up landing squarely on ‘Look, see, I’m making even more money than I was at the last one’.

If you want to chase the money and make your career about making sure that you’re a woman that’s getting paid equally as a man, then keep doing what you’re doing but don’t expect drastically different results from what you’re seeing. I’m not saying that you or any other woman doesn’t deserve to get equal compensation, because that’s not it at all. I would say the same to any man or woman, that if you’re focused squarely on the money, you’re going to have a drastically reduced likeihood of also being happy at your job. Some people can find both, and if they do, then I’d say hold onto that job as long as you can, but I’ve got to tell you that even a mouse learns after running down the same dead end path in a maze that the eventually need to try a new path.

You’re smart. Smart enough that there are many doors in front of you that you can open. I guess the question is how long are you going to keep opening the same one?

I suspect like me you’re a worrier and overthinker at the core and that’s not going to change ever. I’m trying to accept this (embrace might be too strong of a word). Maybe if I was a 1%er making $300k or whatever that might change, but a) it also might not and b) that is just never going to happen anyway, so I’m not going to think about it. I think a lot about how the hell we’re going to afford a family. If he makes $40k all his life and I’m the breadwinner on an average to decent salary how will this work?

I don’t know if it’s in us to accept uncertainty and to not strive for more. Maybe it’s not. But I do know that there are healthy limits – I’m working on finding my equilibrium and i hope you can find yours.

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About Me

The anti-minimalist: I'm the absolute worst with money. I have a shopping addiction. That's exactly why this blog exists. HECC is not a typical personal finance blog. I started it in 2007 to hold myself accountable for binge spending, a dropping networth, and lack of overall fiscal literacy. 10 years later, had achieved a networth of over $500k. Now my goal is to hit $1M by 40. Recently married and with my first kid on the way, things are about to get... interesting. I write about the intersection of mental health and money, spending & investing, and millennial personal finance.